|
Some would say that I am an overachiever. Maybe they are right. I went to a good school and got a good job right out of college. I married my high school sweetheart and settled down to raise a family. At the ripe old age of thirty-two, I had recently been promoted to the position of corporate manger for the claims and reinsurance division of one of the country’s largest insurance firms. People all across the country had to answer to me. Every day, I leave my comfortable home, wife, and three kids out in Hoffman Estates and head into downtown Chicago. I have a good life, love my wife and children, and am proud the career I have carved out. Until a few months ago, I thought I had it all.
Three months back, I was making my way home after entertaining a client with a night on the town. I dropped my inebriated but happy client off at his hotel on Wacker Drive and started home. I was a little drunk, but figured if I was careful I could make it home, sleep it off, and still make it in for my nine o’clock conference call. Unfortunately, I was a little drunker than I thought and found myself on the south side. While making my way down Harlem Avenue, I lost control of the car and ended up wrapping it around a light pole like a bow around a Christmas present. Somehow, I did this without getting even a scratch.
When the cops arrived on the scene, it didn’t take them long to figure out the accident was caused by the fact I was way past the legal limit. They also figured out fairly quick that I was not hurt and that there was no reason to call for medical attention. Trying to bribe them into overlooking my inebriated state didn’t exactly help the situation. Instead of taking me home, they decided to transport me directly to the Cook County Jail. There I was booked on a charge of DUI and tossed into the holding cell with about thirty other men.
Now, I had never been in a jail in my life. And the guys in that cell did not look a lot like the professionals that I routinely met across the boardroom conference table. In short, I was like a sheep that had walked into the proverbial den loaded with a pack of wolves. And some of them were already smacking their lips.
Hoping to avoid any trouble, I tried to ignore the whistles and calls of “come here baby”, “mmmm, fresh meat”, and “I got something to help you pass the time, college boy”. While most of the men looked me over and dismissed me, a few of them started to close in. Before I knew it, I was down at one end of the holding cell, with nine or ten of the men. A quick look around revealed that the guards were few and far between at two in the morning, and were not really all that concerned about what was going on in the cell. While seven of the men positioned themselves so as to block the view, two of the roughest looking came closer. Both of them were easily over six feet tall and loaded down with muscles. Each man was rubbing the bulge in the front of his jeans, and the effort was obviously meant to let me know they were packing plenty. I could easily read the meaning of the look in their eyes and the smile on their lips. One of them looked me up and down and said “I think you want some cock, boy. I got a hard dick right now that will keep you occupied”. While he spoke, his partner pushed me to my knees and grabbed my hair. As I opened my mouth to yell, I heard a zipper go down and suddenly my mouth was full of hard dick.
“My name is Clay and you are about to find out how hard Clay can get. Now suck my dick, you son of a bitch”, he growled and began to face fuck me. I knew that to try to fight would only make it worse, so I tried to time the action of getting a breath when he pulled back and before he rammed his eight thick inches back down my throat. His buddy held my hands behind my back, making sure I could not get out of the way. I had no choice but to withstand thrust after thrust into my raw throat. After what seemed like an eternity, I felt Clay’s cock jerk, and he let out a loud groan. I fairly choked as he emptied his load down my throat.
Not to be outdone, Clay switched places with his buddy and I found myself with a new dick heading for my mouth. This one was a little shorter, but just as thick. He also had foreskin that had not been washed recently. I gagged as he slid his unwashed dick into my mouth. He laughed and said “you like that skin on John’s dick, don’t you, cocksucker? Here, let me peel it back and you can lick the cheese off my dick.” With that, he retracted the sheath and forced me to lick off the thick white coating that covered his dick head. Once John was clean, he resumed his raping of my mouth and throat. He came more quickly than Clay, and I hoped the ordeal was all over.
However, these two were not done with me. Clay was hard all over again and announced that since one of my holes had been broken in, he was going to break in the other hole. He presented his cock to me again and said “Suck me some more, you little fuck, and make sure you get it nice and wet. Coz my dick is going in your ass in a few minutes, and you don’t look like the type who can stand a dry fuck.”
It was obvious that the guards were not going to be any help at all. The crowd blocking the view of the corner were all facing away from us, talking in small groups as if nothing was going on. I knew that if I yelled out, I would be dead before the first guard could even get to the cell door. Scared as hell, I did as I was told. Way too soon, I heard the words I was dreading “okay you little fucker, drop your pants and bend over the bench.
Pulling down my slacks, I felt a finger enter my ass. Clay must have decided to take a little pity on me, because I heard him spit on his finger and work the spittle into my hole. At first, his finger hurt like hell, but slowly I felt my sphincter muscles open a little and the pain began to subside. That lasted only a minute, as he took out his finger, set the head of his dick against my asshole and plunged in.
Without thinking, I let out a yell. John was right there to stifle my yell with his own dick, now hard again after watching his cellmate prepare me for fucking. After keeping still for a moment, I felt Clay’s cock began to move in and out of me. Slowly the pain began to subside as the mix of spittle and Clay’s precum provided a little lubrication for my now sore asshole. Little by little, I found that I could stand the pressure. At the same time, I was now having to suck on John’s dick a second time.
By the time that my asshole was opened up, I heard ragged breathing coming from behind. “You’re a hot little piece of ass, you know that, bitch? You got me hard twice and you are gonna make me cum twice. Yeah, baby, you are a great bitch. You better hope you stay in here a long time, coz I’ll keep you satisfied, you cocksucking office boy.” It was obvious that Clay was about to shoot his load up my ass. With another groan, he cut loose. I felt warm jizz flood my ass. As he pulled out, I felt the liquid run out of my hole and down my legs.
John pulled out of my mouth and informed me it was his turn, now that my ass was loosened up. With that, he moved around behind me and shoved his dick into my still quivering hole and began to fuck me hard and fast. This second time hurt a lot less than the first, and I was able to grit my teeth and stand it until he finished. To my surprise, I felt my own dick begin to grow hard and finally just as John shot his load into my ass, I released a load of my own.
After both of them were finished with me, they pulled me up on the bench and sat down beside me. Slowly, I got the strength back into my legs and was able to begin pulling my shorts and pants back up. They watched in silence while I got myself back together, then pulled me back down on the bench between them.
“Keep one thing in mind, you little man whore” Clay whispered in my ear. “If you say one word about the fun the three of us had tonight, I’ll track you down and slit you open like a pig in a slaughterhouse. Then I’ll fuck you again and use your own blood for the lube. You got that, bitch?”
Not trusting myself to talk, I just nodded and sat still. They each gave me a kiss on the cheek and a slap on the back before moving in with the groups of men standing around the cell. After a time, everyone lost interest and left me alone. For the next two hours, I sat alone on the bench, not daring to look at Clay or John, or any of the other men in the cell. Finally, a guard announced my name and let me out of the cell. My wife had arrived and taken care of the bail. I was free to go.
My wife took my silence on the way home to be embarrassment for getting drunk and wrecking the car. She never said a word when I took a long hot shower and told her to throw away the clothes I had worn that night. She called the office and told them I had been in an accident and would not be in that day, without getting into a lot of details. I spent most of the day working through the fact that I had been raped not once, but four times, twice in my mouth and twice in my ass. And that before it was over with, I was starting to like it.
It has been three months since that night. Life is back to normal and on the surface, everything seems to be as it should be. But now and then I think I catch a glimpse of Clay or John out of the corner of my eye. When I turn, they are never there, but I can’t help but think for a minute that I have not seen the last of them. For some reason, that almost brings a smile to my lips.
|
My Naughty Extreme Stories 
